The airwaves were riddled with scratches, scribbles, and juggling, whether on rock stations (Sublime’s “Doin’ Time,” Limp Bizkit’s desecration of “Faith,” the radio edit of Everlast’s “What It’s Like”) or pop (“I Want You Back,” “Are You Jimmy Ray?,” even fucking “MMMBop”). So it didn’t occur to me—sitting on my bed, taping the radio debut of “Every Morning,” so deeply alone—that Sugar Ray had undertaken something moderately risky. The song was wimpy, no doubt: built on a frame of acoustic guitars, chords not so much strummed as hacked out, with a positively dreamy post-chorus. But DJ Homicide was there—and with ad-libs, no less—so all was right with the world.

But everyone else, including Sugar Ray themselves, understood that 14:59 (which dropped 20 years ago last Friday) was a desperate push to prolong the success wrought by their 1997 hit “Fly.” Reviewers raced to see who would be first to explain the album’s title, its Warhol nod head-thuddingly obvious even then. (Only now, in the Age of Twitter, has Andy’s maxim come true.) But the gambit worked. 14:59 went triple-platinum in less than two years and spawned three Top 40 hits. It also propelled lead singer Mark McGrath into a lucrative new life as a television personality, a path later travelled by the likes of Benji Madden and Adam Levine—though they haven’t matched the sheer volume of his work.

It’s a tidy narrative—band makes pop move at the height of major-label foolishness, charismatic frontperson diversifies his entertainment portfolio. But no one truly understood at the time that 14:59 was a leap from a plunging plane. And though McGrath made a cushy landing, he had every inclination to ride the crash out. He grew up a Newport Beach transplant with a Johnny Rotten jones: “In ‘83-’84, I just wanted to be in a band and play Sex Pistols, Judas Priest, Blondie covers around a keg,” he once told Rolling StoneHe soon got his chance. His classmates’ band was your typical white middle-class covers act (they were called the Tories, for God’s sake) and their boys-just-wanna-have-fun aesthetic meshed well with McGrath’s.

Soon enough, they changed their name to something more palatable (Shrinky Dinx), but kept their fratty vibe. McGrath quit for a time, but a truce brokered by good friend Joseph McGinty Nichol brought the band back together, and Nichol (now known simply as McG) directed a music video that got Shrinky Dinx signed to Atlantic. (The song was called “Caboose,” an unholy combination of glam metal and rap-rock.)

In 1995, the newly-rechristened Sugar Ray (the makers of Shrinky Dinks had pitched a fit) released their first record, Lemonade and Brownies. It is rancid. There’s a track about freeing Mike Tyson; another is called “Big Black Woman.” If you’re feeling generous, the stylistic diversity (talkbox-laden rap-metal, psychobilly, West Coast R&B creeping) speaks to a decently omnivorous taste. If not, it’s a band figuring out what shit’s gonna stick. The album was produced by McG and DJ Lethal (then of House of Pain, later of Limp Bizkit), but Lethal didn’t want to tour with the band, so he recommended a friend: Pasadena’s Craig “DJ Homicide” Bullock, who did the group a huge solid by signing on full-time.

For the next record (of course there was a next record, this was a gilded age), Sugar Ray got a new producer (David Kahne, whom the band knew from his work with Sublime) and a new focus: aggro pop-thrash and rap-rock. This was fine with McGrath, who basically wanted to be Korn, but his bandmates knew something was missing, and the resulting tension caused Mark to bail on the recording session for a while. While he was gone, the rest of the band banged out a trebly jam with chicken-scratch, TK Records-style guitar and a single couplet: “I just want to fly/Put your arms around me, baby.” Persuaded to flesh it out, McGrath half-heartedly threw in lyrical snippets from the Beatles (“who knows how long I loved you”), Gilbert O’Sullivan (“my mother, God rest her soul”), and Killing Joke (the bit about statues crumbling). Hardly the most gifted vocalist, he was fronting the mix like never before (though he did have help from DJ legend Super Cat, who was flown in from Jamaica because it was, again, a gilded age).

“Fly” was the first single from 1997’s Floored, and it was a smash: It topped Billboard’s Modern Rock Tracks chart for two months, and also hit No. 1 on the Hot 100 Airplay chart. There are a few hundred thousand people (I’m one) for whom the song is, essentially, summer. Right before rap-rock became a juggernaut, McGrath and company—who, I cannot stress enough, used to be called Shrinky Dinx—pivoted to straight pop. Perhaps to underscore the perversity of his resistance, Mark spent the time between Floored and 14:59 appearing on VH1’s Jeff Probst-hosted Rock & Roll Jeopardy!, cleaning Joe Walsh’s clock on the way to three convincing wins.

Suddenly, McGrath had changed his tune. “I've always judged a band being historically significant by having a marked certified record,” he said during the recording of 14:59. “We'll pull out our Sebadoh records if you want us to. We'll talk ‘indie,’ but it doesn't interest us.” Kahne returned behind the boards, and he coaxed McGrath into vocal competence. Lead single “Every Morning” was a “Sweet Jane” rip with acoustic turnarounds that sounded like a high schooler practicing “Fly.” It hit the Top 10, as did “Someday,” which upped the haziness with guitar wash and introduced an honest-to-God countermelody. And even though “Falls Apart” sounded like a pop-punk song stranded in a blizzard McGrath’s raspy vulnerability nudged that third single into the Top 30.

The record was filled out with the usual moves. There was a pop cover (Steve Miller Band’s “Abracadabra,” the fullest-sounding thing on here), a Beach Boys homage (“Even Though”), a song dredged up from the time of the Tories (“Ode to the Lonely Hearted”). Toasting was handled this go-round by KRS-One, who had an album coming out that spring, and just kind of wanders around the BDP-sampling “Live & Direct.”

So Sugar Ray was never going to be Korn. But Korn didn’t open the California leg of the Stones’ No Security tour. Despite their beercan-chucking antics, the band had always been game for promotion: McGrath once credited a second chance from their label to an appearance on Howard Stern’s radio show, where they covered a couple songs from Stern’s old garage-rock band. They extended their time in the sun with cameos in Fathers’ Day, Scooby-Doo, and The Drew Carey Show; the requisite appearances at music award shows; and opening for KISS. (“We always kind of believed in the KISS/David Lee Roth kind of philosophy for Sugar Ray,” stickman Stan Frazier told Modern Drummer. “We just want to entertain people.”)

By now firmly in the land of Adult Alternative, Sugar Ray mustered one more hit (2001’s “When It’s Over,” a strummy midtempo pop-rocker, natch). But McGrath, a USC communications major and conventionally attractive person, had begun parlaying award-presentation and VH1 talking-head spots into his next second career. He hosted Don’t Forget the Lyrics! and Killer Karaoke; acted on Law & Order: SVU and the sequels to both Sharknado and Joe Dirt; and spent a number of years as a co-host on Extra. Oh, and he was on Team John Rich during season 4 of Celebrity Apprentice. (“How far it will go, I don’t know,” he said in 2015 of Donald Trump’s presidential run. “I doubt he will even make it to... I envision him dropping out soon.”)

After two more albums, Sugar Ray transitioned to a touring concern. Their time on the charts bought them time enough to participate in the ’90s revival. (Well, McGrath and founding guitarist Rodney Sheppard: DJ Homicide left after running out of ways to garland fluffy pop-rock, and Frazier and bassist Murphy Karges alleged in a lawsuit that they were frozen out of the group.) Two decades after their biggest success, Sugar Ray are just one more ingredient in a puree of alt-rock nostalgia. They’ve toured with Eve 6 and Better Than Ezra; McGrath popped up at a Smashing Pumpkins show last year to sing “Fly” and thank Billy Corgan for being “the Brian Wilson of my generation.”